


Winn on a Whim

by TheForrestofFanfic



Category: Supergirl (TV 2015)
Genre: Caring Winn, Cute, F/M, Fluff, Insecure Alex
Language: English
Status: Completed
Published: 2016-09-16
Updated: 2017-01-27
Packaged: 2018-08-15 09:51:27
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 4,889
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8051734
Author URL: https://archiveofourown.org/users/TheForrestofFanfic/pseuds/TheForrestofFanfic
Summary: HOLD UP! Look I know you've seen the pairing and maybe instantly ready to scroll down but give it a chance their cute and awkward and you might enjoy it. FLUFF!Guys I'm getting some comments about shipping Alex who has now been confirmed as a lesbian with Winn. I'd just like to stress I didn't know she was going to be gay when I wrote this but nevertheless this is an interesting pairing and I'm going to follow through with it - don't like, don't read. Thanks!





	1. Awkward

**Author's Note:**

> AN: First Supergirl fanfic for me! Yay! 
> 
> I’m only up to episode 12 so no spoilers!
> 
> Post Strange visitor from another planet AU!

He didn’t know what he’d expected to happen when he knocked on the door but it definitely wasn’t what he came face to face with.

“Winn.” It was Kara’s adoptive older sister, Alex. She wore a pair of light-grey baggy sweats and a white vest – clothes that he definitely wouldn’t associate with the strong, capable Alex Danvers.

“Uh Alex? Hey is Kara home?” _Well, this is awkward_ he thought to himself as he smiled the best he could while she seemed to scan him like a new kind of alien.

“No not right now, she’s saving some campers from a forest fire.” Her eyes were downcast as she moved to let him in.

“Are you okay Alex? I know we don’t talk much but you know we all need a friend sometimes.” She smiles and chuckles a little but it’s not in her eyes.

“Yeah I’m fine Winn thank you.” Winn knew she was lying; she wrinkled her nose just like Kara does when she lied.

“Yeah I know your sister better than I know anyone in the entire world so I’m gonna know when our lying.” He quips.

“Well, I know you very well too - thanks to everything Kara tells me - and I know that now you know something is up you’re not going to leave, are you?” She raises her eyebrows as she sits and he takes that as an invitation to join her.

“It’s amazing how well we know each other through your sister.” He smiles but it’s weak.

“How are you holding up?” Alex asks and whether it’s out of pity or politeness Winn can’t tell.

“I’ve been in the friend zone since the moment she walked into Catco and met me. I think I can handle not being in that limbo any longer.” They share a laugh and Winn notices the cookie dough ice cream on the table.

“Don’t touch it.” Alex fixes him with a glare while Winn grins and quickly reaches for the tub of ice cream but it’s all over too quickly as his arm is quickly twisted behind his back.

“Okay okay, you’re sister isn’t the only strong one.” He taps on the sofa like it were some kind of wrestling match. He turns only to be handed a tub of ice cream marked ‘Kara’, its strawberry ripple. It’s also his favourite.

“Have it.” She says as she throws herself back onto the sofa digging into the contents of the tub.

“But it’s Kara’s I don’t want to be on the receiving end of her wrath.” He’s about to get up and put it back on the fridge when Alex props her legs up onto Winn.

“And now you have no choice. She can always get another.” Still unconvinced Winn goes to put the ice cream down when Alex fixes him with yet another glare and remembering what happened just a few seconds ago he quickly opens the tub and begins to eat.

“So what is your problem Alex?” Winn said between mouthfuls not forgetting the sad looks Alex had been giving earlier.

“Well, no it’s stupid. Don’t worry about it.” She waves her hands pushing away the thought from the conversation.

“No, no I want to hear it. I doubt it’s stupid.” He sat up and looked at her and his genuine eyes bore into hers and she just spilled right out in front of him.

“Well I feel like I’m getting overshadowed by Kara at work and-”

“Who isn’t overshadowed by Kara, she’s Supergirl.” Winn laughs but catches a potential glare before gesturing for her to carry on.

“Thank you. It’s not like I’m jealous or anything. It’s just that I spent years of my life training in that facility, years gaining enough experience to be respected and then to be second in command but all Kara had to do was turn up and she was already better than me. Am I a bad person?” Alex stares straight at Winn and he just smiles and laughs.

“No Alex you’re just human. You just wanted her to go through the same vigorous process you did and because she didn’t have to you don’t think that you will be as valuable to the DEO as her.” Alex’s head tilted slightly.

“How on…did…figure…out?” She said taking three bites one after the other.

“I’m sorry?” He grinned as she swiped the ice cream off her mouth using the spoon.

“How on earth did you figure that out?” She repeated.

“Because I felt the same way. She could do all these things at Catco because of her powers and I had to work to get myself as high up as I am and sometimes I wish that she knew what normal life was like for us.” He tentatively held her shoulder in comfort.

“Thank you Winn.” Alex yawned and moved to lay on Winn’s side much to his surprise.

“What for?” He asks cautiously.

“For not finding Kara tonight.”


	2. Breakfast at Noonan's

**Notes for the Chapter:**

> So sorry for the long wait - just had absolutely no motivation for a few weeks! Sorry, hope you enjoy!

Alex strolled into Noonan’s scanning the few that were there in the morning. She hadn’t been on a date in almost two years since Kara had begun to work at the DEO. It almost felt new to her – she had no real idea of how to act anymore. Alex wasn’t sure why Winn wanted to have their first date in the morning – it was such a hassle to wake up early and apply makeup as well as choosing the perfect outfit.

Oh God she sounded like Kara when she went on her date with Jimmy…

Pushing that horrible thought from her mind she walked into the centre of the café. Alex wore a brown leather jacket over a plain black v-neck top and a pair of high waisted jeans with a pair of white trainers. Her hair was its normal bob style though she did wear a necklace given to her by Kara on her 18th birthday with the letters A&K engraved in a kite shaped, rose-gold charm.

Once, before the DEO she would have been wearing a short skirt, crop top and high heels but she wasn’t 16 anymore and she had a little more self respect than that. Alex searched for the familiar face and instantly smiled when she found her target, Winn Schott Jr. He stood and it was clear to her he had made an effort this morning – he probably spent more time pruning than she.

“Hey Alex!” He stood and pulled out a chair for her, she took it politely and thanked him. He wore a crisp, white shirt, buttons done all the way up and a pair of shiny black shoes. He also had on a pair of blue denim jeans with a thick brown belt across his waist – _was that a superman belt buckle?_

“I can pull out my own chair.” She said confidently. She’d been an agent at the DEO and had fought countless criminals – Alex could handle a chair.

“Of course you can, you’re the most capable person I know but it’s gentlemanly, isn’t it?” He grinned widely – _it’s cute –_ she thought to herself.

“I thought it was dead but you have single-handedly resurrected chivalry.” She quipped. They chuckled and Alex raised her hand to the waiter who quickly came over to take their order.

“Welcome to Noonan’s, what would you like?” The waiter – a poster boy for optimism and normality – clutched his pen ready to take down their order.

“Ladies first.” Winn smiled taking a fleeting look at Alex before scanning the menu line by line. Her eyes narrowed – it was kind of cheeky the way he directed her, it was almost like a command disguised in chivalry, she liked it a lot.

“Okay, I’ll just have a latte and banana cinnamon waffles please.”

“Hmm nice choice.” Winn complimented still not taking his eyes from the menu. “I’ll just have the usual, thank you.” The waiter took the menus and left the two of them alone.

“The usual?” Alex asked.

“Omelette and orange juice.” Winn clarified.

“Orange juice? What are you six?” Alex teased.

“Ha…yeah.” Winn looked away and the mood changed. It reminded Alex of that night three days ago when she had looked away from him and he’d made her feel better and it had led to this date.

“Umm Winn, what’s wrong? I was only joking.” Alex placed her hand tentatively over Winn’s.

“Sorry, it’s stupid but when my dad used to bring me here when I was a kid and he wasn’t, well, a murderer, I’d always have the same meal for breakfast and I guess I could never really let go.” He smiled sadly and swiftly wiped a stray tear from his eye. “Sorry, I never usually cry on a date.” They laughed and Winn looked down at their now intertwined hands then up at Alex.

“I haven’t dated in a long time.” She confessed as she wrapped the leather jacket a little tighter around herself.

“Don’t worry I have and I suck at it.” He laughed at his own self deprecation while she only smiled slightly.

“Oh come on you have to laugh otherwise it’s just sad.” He grinned as he took a sip of orange juice.

“Ha ha.” She feigned but they both broke out into fits of giggles.

They fell in to light conversation about Alex and the DEO and Winn and Catco, they spoke little about family other than Kara as both did not have so good back stories when it came to family – for different reasons of course. Before long it had been two hours and Alex was late to work.

“Oh crap! I’m an hour late!” Winn’s mouth dropped.

“Damn! Me too!” They both grabbed their coats, reached for their wallets and simultaneously threw twenty dollars on the table.

“Hey I’ll pay, you’ve been the gentleman and now I’ll pay for your meal.” Though reluctant Winn pulled his dollar notes from the table and walked out of Noonan’s with Alex.

“I’m getting the tab next time.” Winn pointed at Alex but he was nowhere near dominative enough for her to feel like she couldn’t just pay for the next one again anyway.

“Of course Winn, you can be the big strong man on the next date.” Alex joked sarcastically.

“So there’s a next date?” Winn grinned widely.

“Yes Winn, this morning was lovely and I would love another lovely moment with you.” She hesitated before eventually kissing him on the cheek. “I need to go.”

“Me too.” Winn blushed and began to turn away towards Catco.

“See you later Winn.” Alex waved slightly.

“Bye Alex.”

Winn chuckled – _who knew I’d be dating Alex Danvers? Sister to the girl I pined for, for so long I wanted Kara but I may have just found someone even more super than super girl!_


	3. Close call

Kara was still watching the kryptonian they’d found after Myriad. Alex was on her own in the apartment – there was only so long you could stare at an unconscious man before it was time to leave but of course Kara wouldn’t. However, Kara did tell her to wait at the apartment rather than going back to her own place downtown likely because she’d want to vent to her about how great it was another person from Krypton had shown up.

“How you holding up?” Winn came through the door and read her expression like he’d been a trained DEO agent his whole life.

“Thought you’d be ogling the new alien.” She joked bitterly.

“Well, I have better things to ogle than aliens from other planets plus I’ve seen these ones before they’re not all that great.” Alex shook her head. He was lying of course but it was sweet, the guy had a superman belt buckle.

“Come here nerd.” His face lit up as he sped around the sofa like a kid on Christmas. She brought him into her arms and they both instantly relaxed.

“You’re beautiful Alex.” He whispered to her in the darkness. The sound of his gentle voice gave her goose bumps.

“As are you Winn.” She lent up and kissed him full on the lips.

“I can’t believe it has been four months since that night in this apartment.” It seemed just like yesterday when he’d come in looking for Kara and had found her instead. Ever since then they’d been dating for two months neither really knowing what this was. They hadn’t even told anyone that they were together.

“When do we start telling people Alex?” Winn wined, his lip pouting slightly.

“I don’t know Winn.” She grinned a little as she turned to straddle his lap. “I thought it was quite hot when we were playing around while Kara or Jimmy were in the next room at Catco.”

“Or when Hank was training at the DEO.” Winn brought Alex’s face close to his. “I think you’re hot all the time Alex, I don’t need a secret to feel that.” He gently brought their lips together relishing her soft pink lips and her wet tongue claiming his.

She moved him so he sat right up against the sofa and straddled him again taking extra care to rub hard against him making him groan. “I don’t need it either – you’re cute enough without it.” She kissed him deeply and they tumbled across the sofa.

It was a blur of arms and hands grabbing whatever skin they could get their hands on, each moaning and groaning when the other found a particularly pleasurable spot. They were lost in each other and yet they had never belonged so well.

Soon their antics made its way to the bedroom – Kara’s bedroom – another thing they liked was having their passionate moments near people or in other people’s apartments, mainly Kara’s. Quickly clothes were stripped off and they were under the protection of the white duvet…

It was 6:00am when Kara finally flew through the windows in to her apartment. She searched the room for her sister who she’d told to wait for her but when her presence wasn’t made known straight away she grew alert. Who had taken her? Was it a new enemy? An old?

“Kara?” Alex stood in the shadows in front of her bed. She looked a little flustered and her heart beat was a little quick but Kara didn’t question it she had so much to talk about with the new Kryptonian in the DEO base.

“Alex don’t do that. You scared me.” The sisters hugged though she felt herself being turned – she put it down to playfulness.

“I’m sorry Kara, come on let’s go and get breakfast.” Alex suddenly said and she raced out pulling Kara with her.

Supergirl would never know of a very naked Winn crawling out of her apartment and back to his own five streets down from Kara’s.

Well at least not yet anyway…


	4. Unexpected

Weeks had still gone by since Winn and Alex had spoken about telling the others and yet Alex had still been evasive and had generally not seemed comfortable with the whole idea and Winn had started to get anxious.

He guessed it was only a matter of time until Alex got bored of him. She was a super cool, strong and independent woman – he knew that perhaps this was only a short term thing for her but he had hoped not. Winn, after all was just a glorified I.T. technician with a passion for coding, how could someone like her really want to stay with a guy like him? The least he could do was ask she break his heart quickly instead of drawing out the pain, he had to leave with what little dignity he had still intact…

He spotted her going into the locker room. He quickly followed suit despite the gender distinction – he knew no one was in there around this time anyway because most were still on shift. He entered swiftly, making his presence known to her. She turned and smiled though it dropped when she saw his own anxious look.

“What’s the matter nerd?” She tried to lighten the mood the best she could.

“I know why you won’t make us public Alex.” He accused and her shocked expression almost confirmed his suspicions.

“But how?” Her brows furrowed as she took a few steps toward him.

“Well, you aren’t exactly discreet Alex.” The room was silent, tension hung in the air and Winn was ready for what he thought was about to come.

“I’m sorry Winn. I just don’t really understand my feelings right now-”

“Well I understand mine!” Winn suddenly shouted. “I know how I feel about you and if you could not bear the thought of not being with a lowly technician then that’s fine, I only wish you had come to me sooner as it would hurt much less.” Winn spun on his heel and stormed out of the room ping away a stray tear as he did so.

“Winn, wait!” Alex called after him. “Damn it!” She sped after him, out the door and down the corridor to the main room. “Winn!” She shouted again, he turned and the down hearted look on his face broke her heart.

Alex knew what she would have to do. In front of all these people, her co workers, her boss - who was looking at the two quizzically – and Mon – El apparently. This wasn’t exactly how she wanted it to come out, if she had her way it may never have at all but she couldn’t let fear stop her. Alex stormed up towards Win, whose face was a mix of confusion and terror, and grabbed his face with both hands and pulled him into a very public kiss.

By his tense body he clearly wasn’t expecting that, by the audible gasps no one else was either and furthermore she definitely didn’t expect to be doing this today. When she broke the kiss Winn still looked just as confused as before.

“But-”

“My feelings that I don’t understand don’t concern you as a person. They concern me because I have not loved someone, I mean loved a man who was not my dad before and I didn’t know what those feelings meant.” She whispered to hm, inches from his face as they breathed the same air, in and out of each other’s lungs.

“You love me?” Winn asked hopefully.

“Yes Winn, I love you… Do you, do you love; love me?”

“Of course I love you Alex.”

Both grinning idiotically they simply stared at each other until Mon called out from behind Winn “Kiss her already you idiot.” They laughed and he captured her lips with his own and her heart leaped high in a single bound. This was right – though they would have to still tell Kara.

Watching the scene from the front of the room, Hank observed the two’s open display of affection angrily.

 

 

 


	5. Unexpected II

**Notes for the Chapter:**

> Sorry guys again for the long wait but college was piling up, my laptop was gone and inspiration was wearing thin. I hope you like the penultimate chapter of this particular series. Thanks!

“Happy six months Winn.” Alex whispered kissing the top of Winn’s forehead after a particularly heated and steamy session in Kara’s bed – again. It’s not as if neither had places (and beds) of their own to have their nightly liaisons it was just far more daring to have them in Kara’s flat.

They had spent the entire weekend in the flat to celebrate them being together for half a year. Many of their colleagues had congratulated them on the occasion and they were grateful – even Alex’s mum had texted her to congratulate the pair. It was strange; it was only six months ago that she hadn’t dated anyone for two years and only a month ago since everyone had found out – besides Kara.

“She must’ve caught on by now?” Winn asked as he huddled into Alex’s side. They had been doing this quite regularly for six months and not once did Kara catch on or at least she never let them know she had.

“I told you Kara sees what she wants to see, always has, that’s why she’s so good at being Supergirl because she only sees good in people.” Alex chuckled as the two lay in darkness.

“We should really tell her now, shouldn’t we?” Alex winced a little as Winn nodded with a knowing smile.

“Yeah we should but of course we can’t because she’s with Barry in another universe.” Winn sighed. After Alex had publically announced the two were together he urged her to include Kara in on the secret now literally everyone else knew but she had been less reluctant.

“Yeah shame.” Alex replied but Winn could tell she wasn’t as sad about it as she seemed.

“Why won’t you tell her?” Winn wondered aloud not longer ready to let her evade him for much longer.

“Do we have to talk about this now? It’s our six months.” She tried to capture his lips but he moved away unwilling to let her divert the conversation to another sexual escapade.

“Yes we do Alex, especially because it’s our six months, it’s unfair on Kara.” Kara was his best friend and Alex’s sister, in reality it should have been her who found out first but Winn reckoned if their stunt at HQ hadn’t happened she would’ve been.

“Okay. I’m, I’m scared to tell her Winn. I’m worried that if I tell her we’ve been secretly dating for six months that she’ll hate me! We tell each other everything, every problem she’s ever had in her life I’ve always known about regardless of how sensitive, emotional or difficult it was to solve. Every mistake I made with boys, alcohol, drugs and every parental struggle I’ve had with my mum she’s been there for. We’re supposed to be sisters and I’ve lied to her for six months.” Alex got up and out of bed as she relentlessly paced up and down in nothing but her bra and panties underwear.

“Didn’t you lie to her for like years though to work and the DEO?” Winn squinted as he tried to figure out what exactly Kara was going to do Alex and perhaps even him.

“Yes but that was under national security oath – I couldn’t even tell her even I wanted too! This is my relationship, something personal and important.” Alex clenched her fists.

“Isn’t saving the world from alien threats important?” Winn joked chuckling away.

“Shut up Winn, this is serious.” Alex looked desperate now and Winn was ready to cut the jokes after seeing Alex so unhinged and worried.

Suddenly, a blue vortex appeared behind them in the middle of the room. It was bright, as if the sun had been brought into the flat and the two shielded their eyes. Then, the one person walked out of the vortex that Alex hoped it wouldn’t be.

Kara floated above the ground in her Supergirl costume and hit the device in her hand causing the vortex behind her to snap shut. The two looked at each other in silence as Kara landed on the wooden floor of her flat, they were screwed.

“Hey Kara.” Winn greeted awkwardly as he sat up bare chest in Kara’s bed.

“Winn! What the hell are you doing in my bed?” She cried confused. “And…half naked?” She said in a far more hopeful tone. Kara shut her eyes tight when he shook his head in reply. “Wait.” Kara opened one eye and saw Alex just her underwear. “Oh my-”

“Kara calm down, we can explain, um-”

“No Alex you, you and Winn, together, in my bed, doing that. What? When? Where? Why? How?” Kara stumbled away from the two and Alex gave Winn a nervous look which he returned with one of confidence.

“Well, we have been…dating for a while and-”

“How long?” Kara whispered.

“Six months today.” Alex replied quietly.

“Six months! You were dating for six months and you didn’t tell me? Either of you?” Kara looked truly hurt and Winn felt eternally terrible.

“Look Kara, it was just fun before, it was kinda hot to keep us a secret from you all and that’s why you didn’t know but we were going to tell you. We were even talking about it just now!” Winn explained which luckily seemed to calm Kara down a little.

“Okay, just um leave please.” Kara told them and the two quickly gathered their clothes and left muttering apologies behind them.


	6. Unexpected III

**Notes for the Chapter:**

> Thank you all so much for your kudos and comments. I'm so glad this fic was largely accepted and I hope you've all enjoyed reading as much as I have writing it. Thanks again for your support!

The alarm clock rang like an air raid siren signalling them to get up and face the impending strike from Kara after she found out about the pair’s relationship the previous night. Winn sprung up and turned off the alarm jerking Alex awake as well. They gave each other a small smile before Alex stepped into the bathroom to shower.

Meanwhile, Winn went to the kitchen and reached for the box of cereal in the cupboard but instead decided he would do something a little different for this morning. God knows they both needed it. He reached instead for the saucepan underneath the sink in the cupboard, doused it in cooking oil and pulled open the fridge and grabbed bacon, egg and sausages. A little longer to prepare than cereal but perhaps needed if they were to get through today.

Alex got out of the shower quickly wrapping herself in a towel that was left on the railing by the door. She also wrapped a second towel around her head to keep her hair dry and left the bathroom. As she opened the door she was welcomed with smells of burning bacon and sounds of sizzling sausages. She grinned at her boyfriend who was unaware of her too focused on cooking.

They said little over breakfast, each caught up in their own thoughts about what they faced when they would walk into the DEO together – usually they never would as to throw Kara off the tracks but of course the game was up and they both still felt awful about never telling her.

“What do you think she’ll say?” Winn finally asked, his nerves finally getting the better of him as he tapped his finger on the glass of orange juice.

“I have no idea. I’ve never really lied to her like this before but if she even says anything at all it’ll be a miracle.” Alex replied poking at her food.

“I told you Alex, we should have told everyone.” Winn looked across the table with an air of resentment for her ignorance and unwillingness to share their relationship publically.

“What? So it’s my fault? You could have told Kara anytime you wanted.” She replied pointing her knife at him.

“You know that’s not true. There is no way you wouldn’t have flipped out if I had.” Winn retorted raising his voice.

“No, you know what let’s not do this. It’s our six months, let’s just go in there and take everything as it comes.” Alex took a deep breath “Agreed?”

“Agreed.” Winn nodded.

The two finished breakfast and left for the DEO…

The two awaited their fates in silence clutching each other’s hands in the elevator on the way up to the DEO headquarters on the top floor. They both stared at the floor numbers wincing a little as each one lit up leading to the very last floor.

“Never thought I’d die so young – I’m still so handsome.” Winn cut through the silence half-joking.

“Shut up nerd.” Alex replied chuckling a little.

Finally, the last floor number lit up and the elevator made a ‘ding’ sound and the doors slowly slid open unveiling the DEO…Or at least they thought it was the DEO. It was quite hard to tell as the place was covered banner and streamers; there was music, laughing and party hats, lots of party hats.

“They’re here!” Mon-El shouted from the back of the DEO. Everyone clapped as the two cautiously stepped in with sheer confusion marking their faces. Suddenly, Kara appeared with a glass of coke in her hand and a big devious grin on her face.

“You already knew didn’t you?” Alex smiled staring at her evil sister.

“Of course I knew. I’m your sister nothing gets passed me. I’m just glad you’ve only used my bed once.” Kara sighed gratefully. Winn and Alex chose not to correct her.

“What is all this Kara?” Winn wondered, shoving his hands in his pockets and awkwardly smiling to his colleagues.

“This is your official six months party.” Hank smiled as he came down the stairs with James Olsen and handed the two a cider for Winn and beer for Alex. The team shared a group hug as the couple laughed at all of what their best friend had put together.

“Congratulations.” They said in unison as everyone in the room applauded for the two while they looked away in embarrassment.

“Thank you by the way.” Mon-El grinned at the two while Hank just sighed.

“For what?” Alex asked.

“For making your relationship public accidentally rather than on purpose, it made me a lot of money and made Hanky here very angry. A double score in my book.” The entire team guffawed at the Daxomite and even Hank joined in.

“To Alex and Winn.” Kara toasted. The two side-glanced each other and kissed as they thought about that awkward first night, the first date and the many after that and they couldn’t wait to make more memories with each other.

 

**Author's Note:**

> What are your thoughts on this? 
> 
> I also think this might be the first pairing between these characters so yay for me! (If it isn’t someone tell me)
> 
> Also I want to improve this so if you have any suggestions please feel free to add them!


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